EP2459667B1 - Procede de transfert de chaleur - Google Patents
Procede de transfert de chaleur Download PDFInfo
- Publication number
- EP2459667B1 EP2459667B1 EP10745303.7A EP10745303A EP2459667B1 EP 2459667 B1 EP2459667 B1 EP 2459667B1 EP 10745303 A EP10745303 A EP 10745303A EP 2459667 B1 EP2459667 B1 EP 2459667B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- process according
- refrigerant
- refrigerant comprises
- trans
- ene
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- 238000000034 method Methods 0.000 title claims description 15
- 239000003507 refrigerant Substances 0.000 claims description 31
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 23
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 claims description 22
- 239000012530 fluid Substances 0.000 claims description 18
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 14
- 230000006835 compression Effects 0.000 claims description 13
- 238000007906 compression Methods 0.000 claims description 13
- AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 claims description 11
- NLOLSXYRJFEOTA-UHFFFAOYSA-N 1,1,1,4,4,4-hexafluorobut-2-ene Chemical compound FC(F)(F)C=CC(F)(F)F NLOLSXYRJFEOTA-UHFFFAOYSA-N 0.000 claims description 10
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 10
- KFUSEUYYWQURPO-OWOJBTEDSA-N trans-1,2-dichloroethene Chemical group Cl\C=C\Cl KFUSEUYYWQURPO-OWOJBTEDSA-N 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- WZLFPVPRZGTCKP-UHFFFAOYSA-N 1,1,1,3,3-pentafluorobutane Chemical compound CC(F)(F)CC(F)(F)F WZLFPVPRZGTCKP-UHFFFAOYSA-N 0.000 claims description 7
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 6
- 239000000314 lubricant Substances 0.000 claims description 6
- MSSNHSVIGIHOJA-UHFFFAOYSA-N pentafluoropropane Chemical compound FC(F)CC(F)(F)F MSSNHSVIGIHOJA-UHFFFAOYSA-N 0.000 claims description 6
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 5
- 239000001569 carbon dioxide Substances 0.000 claims description 5
- 230000005494 condensation Effects 0.000 claims description 5
- 238000009833 condensation Methods 0.000 claims description 5
- 229930195733 hydrocarbon Natural products 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 238000001704 evaporation Methods 0.000 claims description 4
- 150000002430 hydrocarbons Chemical class 0.000 claims description 4
- 239000003381 stabilizer Substances 0.000 claims description 4
- 150000002170 ethers Chemical class 0.000 claims description 3
- 230000008020 evaporation Effects 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- 229920001774 Perfluoroether Polymers 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 claims description 2
- 229920001515 polyalkylene glycol Polymers 0.000 claims description 2
- 229920001289 polyvinyl ether Polymers 0.000 claims description 2
- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 claims 2
- 239000004215 Carbon black (E152) Substances 0.000 claims 1
- 229920005862 polyol Polymers 0.000 claims 1
- -1 polyol ester Chemical class 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 15
- LVGUZGTVOIAKKC-UHFFFAOYSA-N 1,1,1,2-tetrafluoroethane Chemical compound FCC(F)(F)F LVGUZGTVOIAKKC-UHFFFAOYSA-N 0.000 description 8
- 239000007788 liquid Substances 0.000 description 4
- YFMFNYKEUDLDTL-UHFFFAOYSA-N 1,1,1,2,3,3,3-heptafluoropropane Chemical compound FC(F)(F)C(F)C(F)(F)F YFMFNYKEUDLDTL-UHFFFAOYSA-N 0.000 description 3
- FDMFUZHCIRHGRG-UHFFFAOYSA-N 3,3,3-trifluoroprop-1-ene Chemical compound FC(F)(F)C=C FDMFUZHCIRHGRG-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 238000004378 air conditioning Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- GTLACDSXYULKMZ-UHFFFAOYSA-N pentafluoroethane Chemical compound FC(F)C(F)(F)F GTLACDSXYULKMZ-UHFFFAOYSA-N 0.000 description 3
- 238000010792 warming Methods 0.000 description 3
- LDTMPQQAWUMPKS-OWOJBTEDSA-N (e)-1-chloro-3,3,3-trifluoroprop-1-ene Chemical compound FC(F)(F)\C=C\Cl LDTMPQQAWUMPKS-OWOJBTEDSA-N 0.000 description 2
- FYIRUPZTYPILDH-UHFFFAOYSA-N 1,1,1,2,3,3-hexafluoropropane Chemical compound FC(F)C(F)C(F)(F)F FYIRUPZTYPILDH-UHFFFAOYSA-N 0.000 description 2
- CVMVAHSMKGITAV-UHFFFAOYSA-N 1,1,1,4,4,5,5,5-octafluoropent-2-ene Chemical compound FC(F)(F)C=CC(F)(F)C(F)(F)F CVMVAHSMKGITAV-UHFFFAOYSA-N 0.000 description 2
- NDMMKOCNFSTXRU-UHFFFAOYSA-N 1,1,2,3,3-pentafluoroprop-1-ene Chemical compound FC(F)C(F)=C(F)F NDMMKOCNFSTXRU-UHFFFAOYSA-N 0.000 description 2
- PGJHURKAWUJHLJ-UHFFFAOYSA-N 1,1,2,3-tetrafluoroprop-1-ene Chemical compound FCC(F)=C(F)F PGJHURKAWUJHLJ-UHFFFAOYSA-N 0.000 description 2
- FXRLMCRCYDHQFW-UHFFFAOYSA-N 2,3,3,3-tetrafluoropropene Chemical compound FC(=C)C(F)(F)F FXRLMCRCYDHQFW-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000013529 heat transfer fluid Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000002105 nanoparticle Substances 0.000 description 2
- 239000010457 zeolite Substances 0.000 description 2
- ICTYZHTZZOUENE-NSCUHMNNSA-N (e)-1,1,1-trifluorobut-2-ene Chemical compound C\C=C\C(F)(F)F ICTYZHTZZOUENE-NSCUHMNNSA-N 0.000 description 1
- CDOOAUSHHFGWSA-OWOJBTEDSA-N (e)-1,3,3,3-tetrafluoroprop-1-ene Chemical compound F\C=C\C(F)(F)F CDOOAUSHHFGWSA-OWOJBTEDSA-N 0.000 description 1
- NLOLSXYRJFEOTA-UPHRSURJSA-N (z)-1,1,1,4,4,4-hexafluorobut-2-ene Chemical compound FC(F)(F)\C=C/C(F)(F)F NLOLSXYRJFEOTA-UPHRSURJSA-N 0.000 description 1
- VWDLXSWESRUSTM-UHFFFAOYSA-N 1,1,1,2,2,3,3-heptakis(fluoromethoxy)propane Chemical compound FCOC(OCF)C(OCF)(OCF)C(OCF)(OCF)OCF VWDLXSWESRUSTM-UHFFFAOYSA-N 0.000 description 1
- RIQRGMUSBYGDBL-UHFFFAOYSA-N 1,1,1,2,2,3,4,5,5,5-decafluoropentane Chemical compound FC(F)(F)C(F)C(F)C(F)(F)C(F)(F)F RIQRGMUSBYGDBL-UHFFFAOYSA-N 0.000 description 1
- FDOPVENYMZRARC-UHFFFAOYSA-N 1,1,1,2,2-pentafluoropropane Chemical compound CC(F)(F)C(F)(F)F FDOPVENYMZRARC-UHFFFAOYSA-N 0.000 description 1
- NSGXIBWMJZWTPY-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropane Chemical compound FC(F)(F)CC(F)(F)F NSGXIBWMJZWTPY-UHFFFAOYSA-N 0.000 description 1
- VKKBJZFVPNUYQL-UHFFFAOYSA-N 1,1,1,4,4-pentafluorobut-2-ene Chemical compound FC(F)C=CC(F)(F)F VKKBJZFVPNUYQL-UHFFFAOYSA-N 0.000 description 1
- AHVCRWLQBFGUKH-UHFFFAOYSA-N 1,1,1,4-tetrafluorobut-2-ene Chemical compound FCC=CC(F)(F)F AHVCRWLQBFGUKH-UHFFFAOYSA-N 0.000 description 1
- QRPMHFKSNFTWQM-UHFFFAOYSA-N 1,1,2,2,3,3-hexafluoro-4-(trifluoromethoxy)butane Chemical compound FC(F)C(F)(F)C(F)(F)COC(F)(F)F QRPMHFKSNFTWQM-UHFFFAOYSA-N 0.000 description 1
- AWTOFSDLNREIFS-UHFFFAOYSA-N 1,1,2,2,3-pentafluoropropane Chemical compound FCC(F)(F)C(F)F AWTOFSDLNREIFS-UHFFFAOYSA-N 0.000 description 1
- YUXNODKRNXNFFO-UHFFFAOYSA-N 1,1,4-trifluorobut-2-ene Chemical compound FCC=CC(F)F YUXNODKRNXNFFO-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical group ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- DDMOUSALMHHKOS-UHFFFAOYSA-N 1,2-dichloro-1,1,2,2-tetrafluoroethane Chemical compound FC(F)(Cl)C(F)(F)Cl DDMOUSALMHHKOS-UHFFFAOYSA-N 0.000 description 1
- HOMDJHGZAAKUQV-UHFFFAOYSA-N 1-(propoxymethoxy)propane Chemical compound CCCOCOCCC HOMDJHGZAAKUQV-UHFFFAOYSA-N 0.000 description 1
- SLLMGLPBJIHXSR-UHFFFAOYSA-N 1-chloro-1,1-difluorobut-2-ene Chemical compound CC=CC(F)(F)Cl SLLMGLPBJIHXSR-UHFFFAOYSA-N 0.000 description 1
- LDTMPQQAWUMPKS-UHFFFAOYSA-N 1-chloro-3,3,3-trifluoroprop-1-ene Chemical class FC(F)(F)C=CCl LDTMPQQAWUMPKS-UHFFFAOYSA-N 0.000 description 1
- STMDPCBYJCIZOD-UHFFFAOYSA-N 2-(2,4-dinitroanilino)-4-methylpentanoic acid Chemical compound CC(C)CC(C(O)=O)NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O STMDPCBYJCIZOD-UHFFFAOYSA-N 0.000 description 1
- YSUQLAYJZDEMOT-UHFFFAOYSA-N 2-(butoxymethyl)oxirane Chemical compound CCCCOCC1CO1 YSUQLAYJZDEMOT-UHFFFAOYSA-N 0.000 description 1
- HJEORQYOUWYAMR-UHFFFAOYSA-N 2-[(2-butylphenoxy)methyl]oxirane Chemical compound CCCCC1=CC=CC=C1OCC1OC1 HJEORQYOUWYAMR-UHFFFAOYSA-N 0.000 description 1
- HSDVRWZKEDRBAG-UHFFFAOYSA-N 2-[1-(oxiran-2-ylmethoxy)hexoxymethyl]oxirane Chemical compound C1OC1COC(CCCCC)OCC1CO1 HSDVRWZKEDRBAG-UHFFFAOYSA-N 0.000 description 1
- SXYHZEQKWNODPB-UHFFFAOYSA-N 2-[difluoro(methoxy)methyl]-1,1,1,2,3,3,3-heptafluoropropane;1,1,1,2,2,3,3,4,4-nonafluoro-4-methoxybutane Chemical compound COC(F)(F)C(F)(F)C(F)(F)C(F)(F)F.COC(F)(F)C(F)(C(F)(F)F)C(F)(F)F SXYHZEQKWNODPB-UHFFFAOYSA-N 0.000 description 1
- OQISUJXQFPPARX-UHFFFAOYSA-N 2-chloro-3,3,3-trifluoroprop-1-ene Chemical compound FC(F)(F)C(Cl)=C OQISUJXQFPPARX-UHFFFAOYSA-N 0.000 description 1
- GCOYJVXNTBXPGM-UHFFFAOYSA-N 4-chloro-1,1,1-trifluorobut-2-ene Chemical compound FC(F)(F)C=CCCl GCOYJVXNTBXPGM-UHFFFAOYSA-N 0.000 description 1
- LRUDIIUSNGCQKF-UHFFFAOYSA-N 5-methyl-1H-benzotriazole Chemical compound C1=C(C)C=CC2=NNN=C21 LRUDIIUSNGCQKF-UHFFFAOYSA-N 0.000 description 1
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 1
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
- 241001644893 Entandrophragma utile Species 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
- BGNXCDMCOKJUMV-UHFFFAOYSA-N Tert-Butylhydroquinone Chemical compound CC(C)(C)C1=CC(O)=CC=C1O BGNXCDMCOKJUMV-UHFFFAOYSA-N 0.000 description 1
- 229910010413 TiO 2 Inorganic materials 0.000 description 1
- 229910021536 Zeolite Inorganic materials 0.000 description 1
- ZVQOOHYFBIDMTQ-UHFFFAOYSA-N [methyl(oxido){1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-lambda(6)-sulfanylidene]cyanamide Chemical compound N#CN=S(C)(=O)C(C)C1=CC=C(C(F)(F)F)N=C1 ZVQOOHYFBIDMTQ-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 150000003851 azoles Chemical class 0.000 description 1
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
- 239000012964 benzotriazole Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- KYKAJFCTULSVSH-UHFFFAOYSA-N chloro(fluoro)methane Chemical compound F[C]Cl KYKAJFCTULSVSH-UHFFFAOYSA-N 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- GVJHHUAWPYXKBD-UHFFFAOYSA-N d-alpha-tocopherol Natural products OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 229940087091 dichlorotetrafluoroethane Drugs 0.000 description 1
- NKDDWNXOKDWJAK-UHFFFAOYSA-N dimethoxymethane Chemical compound COCOC NKDDWNXOKDWJAK-UHFFFAOYSA-N 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002118 epoxides Chemical class 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 238000013021 overheating Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 238000005057 refrigeration Methods 0.000 description 1
- 230000035807 sensation Effects 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 235000010384 tocopherol Nutrition 0.000 description 1
- 229960001295 tocopherol Drugs 0.000 description 1
- 229930003799 tocopherol Natural products 0.000 description 1
- 239000011732 tocopherol Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K5/00—Heat-transfer, heat-exchange or heat-storage materials, e.g. refrigerants; Materials for the production of heat or cold by chemical reactions other than by combustion
- C09K5/02—Materials undergoing a change of physical state when used
- C09K5/04—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa
- C09K5/041—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa for compression-type refrigeration systems
- C09K5/044—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa for compression-type refrigeration systems comprising halogenated compounds
- C09K5/045—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa for compression-type refrigeration systems comprising halogenated compounds containing only fluorine as halogen
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2205/00—Aspects relating to compounds used in compression type refrigeration systems
- C09K2205/10—Components
- C09K2205/106—Carbon dioxide
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2205/00—Aspects relating to compounds used in compression type refrigeration systems
- C09K2205/10—Components
- C09K2205/11—Ethers
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2205/00—Aspects relating to compounds used in compression type refrigeration systems
- C09K2205/10—Components
- C09K2205/11—Ethers
- C09K2205/112—Halogenated ethers
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2205/00—Aspects relating to compounds used in compression type refrigeration systems
- C09K2205/10—Components
- C09K2205/12—Hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2205/00—Aspects relating to compounds used in compression type refrigeration systems
- C09K2205/10—Components
- C09K2205/12—Hydrocarbons
- C09K2205/122—Halogenated hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2205/00—Aspects relating to compounds used in compression type refrigeration systems
- C09K2205/10—Components
- C09K2205/12—Hydrocarbons
- C09K2205/126—Unsaturated fluorinated hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
- C10M2201/06—Metal compounds
- C10M2201/062—Oxides; Hydroxides; Carbonates or bicarbonates
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
- C10M2201/10—Compounds containing silicon
- C10M2201/102—Silicates
- C10M2201/103—Clays; Mica; Zeolites
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
- C10M2203/02—Well-defined aliphatic compounds
- C10M2203/022—Well-defined aliphatic compounds saturated
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
- C10M2203/06—Well-defined aromatic compounds
- C10M2203/065—Well-defined aromatic compounds used as base material
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
- C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
- C10M2205/028—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers containing aliphatic monomers having more than four carbon atoms
- C10M2205/0285—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers containing aliphatic monomers having more than four carbon atoms used as base material
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
- C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2209/04—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to an alcohol or ester thereof; bound to an aldehyde, ketonic, ether, ketal or acetal radical
- C10M2209/043—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to an alcohol or ester thereof; bound to an aldehyde, ketonic, ether, ketal or acetal radical used as base material
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
- C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2209/102—Polyesters
- C10M2209/1023—Polyesters used as base material
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
- C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
- C10M2209/1033—Polyethers, i.e. containing di- or higher polyoxyalkylene groups used as base material
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
- C10M2211/02—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen and halogen only
- C10M2211/022—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen and halogen only aliphatic
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
- C10N2020/01—Physico-chemical properties
- C10N2020/055—Particles related characteristics
- C10N2020/06—Particles of special shape or size
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/30—Refrigerators lubricants or compressors lubricants
Definitions
- the present invention relates to a method for transferring heat using a composition containing hydrofluoroolefins. More particularly, it relates to the use of a composition containing hydrofluoroolefins in heat pumps.
- ODP ozone depletion potential
- HFC-134a hydrofluorocarbon (1,1,1,2 tetrafluoroethane: HFC-134a ), less harmful for the ozone layer.
- CFC-12 chlorofluorocarbon
- HFC-134a hydrofluorocarbon (1,1,1,2 tetrafluoroethane: HFC-134a )
- GWP 1300
- the contribution to the greenhouse effect of a fluid is quantified by a criterion, the GWP (Global Warming Potentials) which summarizes the warming potential by taking a reference value of 1 for carbon dioxide.
- Carbon dioxide being non-toxic, non-flammable and having a very low GWP, has been proposed as refrigerant air conditioning systems replacing HFC-134a.
- the use of carbon dioxide has several disadvantages, particularly related to the very high pressure of its implementation as a refrigerant in existing devices and technologies.
- compositions comprising at least one fluoroalkene having three or four carbon atoms, especially pentafluoropropene and tetrafluoropropene, preferably having a GWP of at most 150, as heat transfer fluids.
- fluorohaloalkenes having 3 to 6 carbon atoms especially tetrafluoropropenes, pentafluoropropenes and chlorotrifluoropropenes have been described as being suitable for use as heat transfer fluid.
- the document WO2007 / 053697 discloses heat transfer fluids comprising fluoroolefins having at least 5 carbon atoms.
- HCFC-114 dichlorotetrafluoroethane
- US 6814884 discloses a composition comprising 1,1,1,3,3-pentafluorobutane (HFC-365mfc) and at least one compound selected from 1,1,1,2-tetrafluoroethane, pentafluoroethane (HFC-125), 1,3,3-pentafluoropropane (HFC-245fa) and 1,1,1,2,3,3,3-heptafluoropropane (HFC-227ea).
- these compounds have a high GWP and have very high compression ratios and temperature slumps compared to HCFC-114
- compositions containing hydrofluoroolefins are particularly suitable as heat transfer fluid in heat pumps, in particular heat pumps operating at high condensing temperature.
- these compositions have a negilizable ODP and a GWP lower than that of existing heat transfer fluids.
- these mixtures have critical temperatures above 150 ° C, thus allowing their use in high temperature heat pumps.
- a heat pump is a thermodynamic device that transfers heat from the coldest environment to the hottest environment.
- the heat pumps used for heating are called compression and the operation is based on the principle of cycle with compression of fluids, called refrigerants.
- These heat pumps operate with compression systems with one or more stages. At a given stage, when the refrigerant is compressed from the gaseous state to the liquid state, an exothermic reaction (condensation) occurs which produces heat. Conversely, if the fluid is expanded from the liquid state to the gaseous state, an endothermic reaction (evaporation) occurs which produces a cold sensation. Everything rests on the change of state of a fluid used in closed circuit.
- Each stage of a compression system comprises (i) an evaporation step during which, in contact with the calories drawn from the environment, the refrigerant, thanks to its low boiling point, changes from the two-phase state (liquid / gas) in the gas state, (ii) a compression step during which the gas of the preceding step is brought to high pressure, (iii) a condensation step during which the gas goes transmit its heat to the heating circuit (warm environment); the refrigerant, always compressed, becomes liquid again and (iv) a relaxation step during which the fluid pressure is reduced. The fluid is ready for a new absorption of calories from the cold environment.
- At least one alkyl group of the hydrofluoroolefin is completely substituted by the fluorine atoms.
- the condensation temperature of the refrigerant is between 70 and 150 ° C, and advantageously between 95 and 140 ° C.
- hydrofluoroolefins of formula (I) there may be mentioned 1,1,1,4,4,4-hexafluorobut-2-ene, 1,1,1,4,4,5,5,5- octafluoro-pent-2-ene, 1,1,1,4-tetrafluorobut-2-ene, 1,1,1,4,4-pentafluorobut-2-ene, 1,1,1,4-trifluorobut-2-ene, 1,1,1-trifluorobut-2-ene, 4-chloro-1,1,1-trifluorobut-2-ene, 4-chloro-4,4-difluorobut-2-ene.
- Preferred hydrofluoroolefins of formula (I) may be in cis or trans form or a mixture of both.
- the refrigerant may comprise at least one compound chosen from hydrofluorocarbons, hydrocarbons, (hydro) fluoroethers, hydrochlorofluoropropenes, hydrofluoropropenes, ethers, methyl, carbon dioxide and trans-1,2-dichloroethylene.
- hydrofluorocarbons mention may in particular be made of 1,1,1,3,3-pentafluorobutane, 1,1,1,2-tetrafluoroethane, pentafluoroethane, 1,1,1,3,3-pentafluoropropane, 1,1,1,3,3-pentafluorobutane and , 1,2,3-pentafluoropropane, 1,1,1,2,2-pentafluoropropane, 1,1,1,3,3,3-hexafluoropropane, 1,1,2,2,3-pentafluoropropane, 1,1,1,3,3-pentafluorobutane, 1,1,1,2,2,3,4,5,5,5-decafluoropentane and 1,1,1,2,3,3,3 -heptafluoropropane.
- Hydrocarbons having at least three carbon atoms are preferred. Five-carbon hydrocarbons such as pentane, isopentane and cyclopentane are particularly preferred.
- hydrofluoroethers there may be mentioned in particular heptafluoromethoxy propane, nonafluoromethoxy butane and nonafluoroethoxy butane.
- Hydrofluoroether is available in several isomeric forms such as 1,1,1,2,2,3,3,4,4-nonafluoro-ethoxybutane, 1,1,1,2,3,3-hexafluoro-2 - (trifluoromethyl) -3-ethoxybutane, 1,1,1,2,2,3,3,4,4-nonafluoro-methoxybutane, 1,1,1,2,3,3-hexafluoro-2- ( trifluoromethyl) -3-methoxybutane, and 1,1,1,2,2,3,3-heptafluoromethoxypropane.
- Preferred hydrofluoropropenes are trifluoropropenes such as 1,1,1-trifluoropropene, tetrafluoropropenes such as 2,3,3,3-tetrafluoropropene (HFO-1234yf), and 1,3,3,3-tetrafluoropropene (cis and / or trans).
- the ethers may be chosen from dimethyl ether, diethyl ether, dimethoxymethane or dipropoxymethane.
- the refrigerant comprises at least one hydrofluoroolefin of formula (I) and at least one hydrofluorocarbon.
- the hydrofluorocarbon chosen is advantageously 1,1,1,3,3-pentafluorobutane and 1,1,1,3,3-pentafluoropropane
- Azeotropic compositions of 1,1,1,4,4,4-hexafluorobut-2-ene or 1,1,1,4,4,5,5,5-octafluoro-pent-2-ene with the formate of methyl, pentane, isopentane, cyclopentane or trans-1,2-dichloroethylene may also be suitable.
- the refrigerant comprises at least 10% by weight of hydrofluoroolefins of formula (I)
- the refrigerant comprises from 40 to 100% by weight of 1,1,1,4,4,4-hexafluorobut-2-ene and from 0 to 60% by weight of at least one compound selected from pentane, isopentane, cyclopentane and trans-1,2, dichloroethylene.
- Particularly preferred refrigerants include those comprising from 60 to 100% by weight of 1,1,1,4,4,4-hexafluorobut-2-ene and from 0 to 40% by weight of cyclopentane, pentane, d isopentane or trans 1,2-dichloroethylene.
- the refrigerant used in the present invention may comprise a hydrofluoroolefin stabilizer.
- the stabilizer represents at most 5% by weight relative to the total composition of the fluid.
- nitromethane ascorbic acid, terephthalic acid, azoles such as tolutriazole or benzotriazole, phenol compounds such as tocopherol, hydroquinone, t-butyl hydroquinone, 2 , 6-di-tert-butyl-4-methylphenol, epoxides (optionally fluorinated or perfluorinated alkyl or alkenyl or aromatic) such as n-butyl glycidyl ether, hexanediol diglycidyl ether, allyl glycidyl ether, butylphenylglycidyl ether, phosphites, phosphates, phosphonates, thiols and lactones.
- epoxides optionally fluorinated or perfluorinated alkyl or alkenyl or aromatic
- the refrigerant used in the process according to the present invention may comprise lubricants such as mineral oil, alkylbenzene, polyalfaolefin, polyalkylene glycol, polyolester and polyvinyl ether.
- Lubricants used with the refrigerant may include nanoparticles to improve the thermal conductivity of the fluid as well as its compatibility with the lubricants. As nanoparticles, mention may in particular be made of Al 2 O 3 or TiO 2 particles.
- Lubricants used with the refrigerant may include zeolite dehumidifying agents. Zeolites absorb water and thus limit corrosion and performance degradation.
- Refrigerant performance under heat pump operating conditions with evaporator temperature maintained at 30 ° C, compressor inlet maintained at 35 ° C and condenser at 90 ° C are given below .
- the COP of the different products is calculated in% of the COP of HCFC114 or R114.
- the binary mixtures (H, J) and (C, J) have a COP, a condenser inlet temperature and a compression ratio equivalent to the value of R114 and these products are quazi-azeotropic with lower temperature slip values. at 2.2 ° C.
- the product J and the mixtures (E, J) have a COP 5% higher than the COP of the reference product (R114).
- Refrigerant performance under heat pump operating conditions with evaporator temperature maintained at 80 ° C, compressor inlet maintained at 85 ° C and condenser at 140 ° C are given below .
- the COP and CAP of the different products are calculated in% of the COP and CAP of R114 respectively
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Physics & Mathematics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Combustion & Propulsion (AREA)
- Thermal Sciences (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Lubricants (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
- La présente invention concerne un procédé de transfert de chaleur à l'aide d'une composition renfermant des hydrofluorooléfines Elle a plus particulièrement pour objet l'utilisation d'une composition renfermant des hydrofluorooléfines dans les pompes à chaleur.
- Les problèmes posés par les substances appauvrissant la couche d'ozone atmosphérique (ODP : ozone depletion potential) ont été traités à Montréal où a été signé le protocole imposant une réduction de la production et de l'utilisation des chlorofluorocarbures (CFC). Ce protocole a fait l'objet d'amendements qui ont imposé l'abandon des CFC et étendu la réglementation à d'autres produits.
- L'industrie de la réfrigération et de la production d'air conditionné a beaucoup investi dans la substitution de ces fluides frigorigènes.
- Dans l'industrie automobile, les systèmes de climatisation des véhicules commercialisés dans de nombreux pays sont passés d'un fluide frigorigène au chlorofluorocarbure (CFC-12) à celui de l'hydrofluorocarbure (1,1,1,2 tetrafluoroéthane : HFC-134a), moins nocif pour la couche d'ozone. Cependant, au regard des objectifs fixés par le protocole de Kyoto, le HFC-134a (GWP = 1300) est considéré comme ayant un pouvoir de réchauffement élevé. La contribution à l'effet de serre d'un fluide est quantifiée par un critère, le GWP (Global Warming Potentials) qui résume le pouvoir de réchauffement en prenant une valeur de référence de 1 pour le dioxyde de carbone.
- Le dioxyde de carbone étant non-toxique, ininflammable et ayant un très faible GWP, a été proposé comme fluide frigorigène des systèmes de climatisation en remplacement du HFC-134a. Toutefois, l'emploi du dioxyde de carbone présente plusieurs inconvénients, notamment liés à la pression très élevée de sa mise en oeuvre en tant que fluide frigorigène dans les appareils et technologies existants.
- Le document
JP 4110388 - Le document
WO2004/037913 divulgue l'utilisation des compositions comprenant au moins un fluoroalcène ayant trois ou quatre atomes de carbone, notamment le pentafluoropropène et le tetrafluoropropène, de préférence ayant un GWP au plus de 150, comme fluides de transfert de chaleur. - Dans le document
WO 2007/002625 , des fluorohalogénoalcènes ayant de 3 à 6 atomes de carbone, notamment les tetrafluoropropènes, les pentafluoropropènes et les chlorotrifluoropropènes ont été décrites comme susceptibles d'être utilisées comme fluide de transfert de chaleur. - Le document
WO2007/053697 décrit des fluides de transfert de chaleur comprenant des fluoorooléfines ayant au moins 5 atomes de carbone. - Dans le domaine des pompes à chaleur, des substituts au dichlorotetrafluoroéthane (HCFC-114), utilisé dans des conditions de température de condensation élevée, ont été proposés. Ainsi, le document
US 6814884 décrit une composition comprenant du 1,1,1,3,3-pentafluorobutane (HFC-365mfc) et au moins un composé choisi parmi le 1,1,1,2 tetrafluoroéthane, le pentafluoroéthane (HFC-125), le 1,1,1,3,3-pentafluoropropane (HFC-245fa) et le 1,1,1,2,3,3,3-heptafluoropropane (HFC-227ea). Cependant, ces composés ont un GWP élevé et présentent des rapports de compression et des glissements de température très élevés par rapport au HCFC-114 - Le document
US 20090049856 décrit des fluides de transfert de chaleur comprenant le 1,1,1,3,3-pentafluoropropane (HFC-245fa), 1,1,1,2,3,3 hexafluoropropane (HFC-236ea ) et le tetrafluoroethane (HFC-134a). Toutefois, ces mélanges présentent des températures à l'entrée du condenseur (sortie compresseur) très élevée, ce qui implique la surchauffe des parties mécaniques et la diminution du rendement globale du compresseur. En outre, les températures critiques de ces mélanges (autour de 110°C) sont inférieures à la température de condensation souhaitée (120 voir 150°C) rendant leur utilisation impossible dans les pompes à chaleur haute température. - Le document
WO2008/134061 décrit un procédé de transfert de chaleur utilisant des compositions comportant du Z-1,1,1,4,4,4-hexafluoro-2--butène - La demanderesse a maintenant découvert que des compositions renfermant des hydrofluorooléfines conviennent tout particulièrement comme fluide de transfert de chaleur dans les pompes à chaleur, en particulier les pompes à chaleur opérant à température de condensation élevée. En outre ces compositions ont un ODP négilgeable et un GWP inférieur à celui des fluides de transfert de chaleur existants. De surcroît, ces mélanges présentent des températures critiques supérieures à 150°C , permettant ainsi leur utilisation dans les pompes à chaleur haute température.
- Une pompe à chaleur est un dispositif thermodynamique permettant de transférer de la chaleur du milieu le plus froid vers le milieu le plus chaud. Les pompes à chaleur employées pour le chauffage sont dites à compression et le fonctionnement est basé sur le principe de cycle à compression de fluides, appelés fluides frigorigènes. Ces pompes à chaleur fonctionnent avec des systèmes à compression comportant un seul ou plusieurs étage(s). A un étage donné, lorsque le fluide frigorigène est comprimé et passe de l'état gazeux à l'état liquide, il se produit une réaction exothermique (condensation) qui produit de la chaleur. A l'inverse, si on détend le fluide en le faisant passer de l'état liquide à l'état gazeux, il se produit une réaction endothermique (évaporation), qui produit une sensation de froid. Tout repose donc sur le changement d'état d'un fluide utilisé en circuit fermé.
- Chaque étage d'un système à compression comprend (i) une étape d'évaporation au cours de laquelle au contact des calories puisées dans l'environnement, le fluide frigorigène, grâce à son faible point d'ébullition, passe de l'état diphasique (liquide/gaz) à l'état de gaz, (ii) une étape de compression au cours de laquelle le gaz de l'étape précédente est porté à haute pression, (iii) une étape de condensation au cours de laquelle le gaz va transmettre sa chaleur au circuit de chauffage (environnement chaud) ; le fluide frigorigène, toujours comprimé, redevient liquide et (iv) une étape de détente au cours de laquelle la pression du fluide est réduite. Le fluide est prêt pour une nouvelle absorption de calories de l'environnement froid.
- La présente invention a pour objet un procédé de transfert de chaleur mettant en oeuvre un système à compression comportant au moins un étage comprenant successivement une étape d'évaporation d'un fluide frigorigène, une étape de compression, une étape de condensation dudit fluide à une température supérieure ou égale à 70°C et une étape de détente dudit fluide caractérisé en ce que le fluide frigorigène comprend au moins une hydrofluorooléfine ayant au moins 4 atomes de carbone représentées par la formule (I) R1CH=CHR2 dans laquelle R1 et R2 représentent indépendamment, des groupements alkyle, ayant de 1 à 6 atomes de carbone, substitués par au moins un atome de fluor, éventuellement par au moins un atome de chlore.
- De préférence, au moins un groupement alkyle de l'hydrofluorooléfine est complètement substitué par les atomes de fluor.
- De préférence, la température de condensation du fluide frigorigène est comprise entre 70 et 150°C , et avantageusement comprise entre 95 et 140°C.
- Comme hydrofluorooléfines de formule (I) particulièrement intéressantes, on peut citer notamment le 1,1,1,4,4,4-hexafluorobut-2-ène, le 1,1,1,4,4,5,5,5-octafluoro-pent-2-ène, le 1,1,1,4-tetrafluorobut-2-ène, le 1,1,1,4,4-pentafluorobut-2-ène, le1,1,4-trifluorobut-2-ène, le 1,1,1-trifluorobut-2-ène, le 4-chloro-1,1,1-trifluorobut-2-ène, le 4-chloro-4,4-difluorobut-2-ene.
- Les hydrofluorooléfines de formule (I) préférées peuvent être sous forme cis ou trans ou mélange des deux.
- Outre les ou l'hydrofluorooléfine(s) de formule (I), le fluide frigorigène peut comprendre au moins un composé choisi parmi les hydrofluorocarbures, les hydrocarbures, les (hydro)fluoroéthers, les hydrochlorofluoropropènes, les hydrofluoropropènes, les éthers, le formate de méthyle, le dioxyde de carbone et le trans-1,2 dichloroéthylène.
- Comme hydrofluorocarbures, on peut citer notamment le 1,1,1,3,3-pentafluorobutane, le 1,1,1,2 tetrafluoroéthane, le pentafluoroéthane, le 1,1,1,3,3-pentafluoropropane, le 1,1,1,2,3-pentafluoropropane, le 1,1,1,2,2-pentafluoropropane, le 1,1,1,3,3,3-hexafluoropropane, le 1,1,2,2,3-pentafluoropropane, le 1,1,1,3,3-pentafluorobutane, le 1,1,1,2,2,3,4,5,5,5-decafluoropentane et le 1,1,1,2,3,3,3-heptafluoropropane.
- Les hydrocarbures, ayant au moins trois atomes de carbone sont préférés. Les hydrocarbures à cinq atomes de carbone tels que le pentane, isopentane, cyclopentane sont particulièrement préférées.
- Les hydrochlorofluoropropenes préférés sont le 2-chloro-3,3,3-trifluoroprop-1-ene, le 1-chloro-3,3,3-trifluoroprop-1-ene, en particulier le trans_1-chloro-3,3,3-trifluoroprop-1-ene.,
- Les hydrofluoroéthers préférés sont ceux ayant de trois à six atomes de carbone.
- Comme hydrofluoroéthers, on peut citer notamment l'heptafluoromethoxy propane, le nonafluoromethoxy butane et le nonafluoroéthoxy butane. L'hydrofluoroéther est disponible sous plusieurs formes isomères tels que le 1,1,1,2,2,3,3,4,4-nonafluoro-éthoxybutane, le 1,1,1,2,3,3 -hexafluoro-2-(trifluorométhyl)-3-éthoxybutane, le 1,1,1,2,2,3,3,4,4-nonafluoro-méthoxybutane, le 1,1,1,2,3,3 -hexafluoro-2-(trifluorométhyl)-3-méthoxybutane, et le 1,1,1,2,2,3,3-heptafluoromethoxypropane.
- Les hydrofluoropropènes préférés sont les trifluoropropènes tel que le 1,1,1-trifluoropropène, les tetrafluoropropènes tels que le 2,3,3,3-tetrafluoropropène (HFO-1234yf), et le 1,3,3,3-tetrafluoropropène (cis et/ou trans).
- Les éthers peuvent être choisis parmi le diméthyléther, le diéthyléther, le diméthoxyméthane ou le dipropoxyméthane.
- De préférence, le fluide frigorigène comprend au moins un hydrofluorooléfine de formule (I) et au moins un hydrofluorocarbure. L'hydrofluorocarbure choisi est avantageusement le 1,1,1,3,3-pentafluorobutane et le 1,1,1,3,3-pentafluoropropane
- Des compositions azéotropiques du 1,1,1,4,4,4-hexafluorobut-2-ène ou du 1,1,1,4,4,5,5,5-octafluoro-pent-2-ène avec le formate de méthyl, le pentane, l'isopentane, le cyclopentane ou le trans-1,2 dichloroéthylène peuvent également convenir.
- De préférence, le fluide frigorigène comprend au moins 10 % en poids d'hydrofluorooléfines de formule (I)
- Selon un mode de réalisation de l'invention, le fluide frigorigène comprend de 40 à 100% en poids de 1,1,1,4,4,4-hexafluorobut-2-ène et de 0 à 60 % en poids d'au moins un composé choisi parmi le pentane, l'isopentane, le cyclopentane et le trans-1,2,dichloroéthylène.
- Comme fluides frigorigènes particulièrement préférés, on peut citer ceux comprenant de 60 à 100 % en poids de 1,1,1,4,4,4-hexafluorobut-2-ène et de 0 à 40 % en poids de cyclopentane , pentane, d'isopentane ou trans 1,2-dichloroéthylène.
- Le fluide frigorigène utilisé dans la présente invention peut comprendre un stabilisant de l'hydrofluorooléfine. Le stabilisant représente au plus 5 % en poids par rapport à la composition totale du fluide.
- Comme stabilisants, on peut citer notamment le nitromethane, l'acide ascorbique, l'acide terephtalique, les azoles tels que le tolutriazole ou le benzotriazole, les composés phénoliques tels que le tocopherol, l'hydroquinone, le t-butyl hydroquinone, le 2,6-di-ter-butyl-4-methylphenol, les epoxydes (alkyl éventuellement fluoré ou perfluoré ou alkenyl ou aromatique) tels que les n-butyl glycidyl ether, hexanediol diglycidyl ether, allyl glycidyl ether, butylphenylglycidyl ether, les phosphites, les phosphates, les phosphonates, les thiols et lactones.
- Le fluide frigorigène utilisé dans le procédé selon la présente invention peut comprendre des lubrifiants tels que l'huile minérale, alkylbenzène, le polyalfaoléfine, le polyalkylène glycol, le polyolester et le polyvinyl éther. Les lubrifiants utilisés avec le fluide frigorigène peuvent comprendre des nanoparticules afin d'améliorer la conductivité thermique du fluide ainsi que sa compatibilité avec les lubrifiants. Comme nanoparticules, on peut citer notamment les particules d'Al2O3 ou de TiO2.
- Les lubrifiants utilisés avec le fluide frigorigène peuvent comprendre des agent de déhumidification type zeolite. Les zeolites absorbent l'eau et ainsi limitent la corrosion et la degradation des performances.
- Dans ce qui suit :
- Evap : évaporateur,
- Cond : condenseur,
- Temp: température,
- Comp: compresseur,
- P: pression,
- Taux : le taux de compression
- COP : coefficient de performance et est défini, lorsqu'il s'agit d'une pompe à chaleur comme étant la puissance chaude utile fournie par le système sur la puissance apportée ou consommée par le système
- CAP : capacité volumétrique, c'est la capacité calorifique de chauffage par unité de volume (kJ/m3)
- % CAP ou COP c'est le rapport de la valeur du CAP ou COP du fluide par rapport à celui obtenu avec le HCFC-114.
- Les performances du fluide frigorigène dans les conditions de fonctionnement de pompe à chaleur avec la température à l'évaporateur maintenue à 30°C, à l'entrée du compresseur maintenue à 35°C et au condenseur à 90°C sont données ci-dessous.
- Le COP des differents produits est calculé en % du COP du HCFC114 ou R114.
- Rendement isentropique du compresseur : 59,3 %
- C
- ISOPENTANE
- E
- trans-1,2 dichloroéthylène
- H
- pentane
- J
- 1,1,1,4,4,4-hexafluorobut-2-ène
- Les résultats montrent une augmentation du COP par rapport au produit de référence (R114).
- Les mélanges binaires (H, J) et (C,J) présentent un COP, une température d'entrée condenseur et un taux de compression équivalents au valeur du R114 et ces produits sont des quazi-azéotropes avec des valeurs de glissement de température inférieur à 2,2°C.
- Le produit J et les mélanges (E,J) présentent un COP 5% supérieur au COP du produit de référence (R114).
- Les performances du fluide frigorigène dans les conditions de fonctionnement de pompe à chaleur avec la température à l'évaporateur maintenue à 80°C, à l'entrée du compresseur maintenue à 85°C et au condenseur à 140°C sont données ci-dessous.
- Le COP et CAP des differents produits sont calculés en % du COP et CAP du R114 respectivement
- Rendement isentropique du compresseur : 59.3 %
- C
- ISOPENTANE
- E
- trans-1,2 dichloroéthylène
- H
- pentane
- J
- 1,1,1,4,4,4-hexafluorobut-2-ène
- Les résultats montrent que le COP des nouveaux produits est largement supérieur au COP de la référence (R114).
Claims (10)
- Procédé de transfert de chaleur mettant en oeuvre un système à compression comportant au moins un étage comprenant successivement une étape d'évaporation d'un fluide frigorigène, une étape de compression, une étape de condensation dudit fluide à une température supérieure ou égale à 70°C et une étape de détente dudit fluide caractérisé en ce que le fluide frigorigène comprend au moins une hydrofluorooléfine ayant au moins 4 atomes de carbone représentées par la formule R1CH=CHR2 dans laquelle R1 et R2 représentent indépendamment, des groupements alkyle, ayant de 1 à 6 atomes de carbone, substitués par au moins un atome de fluor, éventuellement par au moins un atome de chlore.
- Procédé selon la revendication 1 caractérisé en ce que la température est comprise entre 70 et 150°C, de préférence entre 95 et 140°C.
- Procédé selon la revendication 1 ou 2 caractérisé en ce que le fluide frigorigène comprend en outre au moins un composé choisi parmi les hydrofluorocarbures, les hydrocarbures, les (hydro)fluoroéthers, les hydrochlorofluoropropènes, les hydrofluoropropènes, les éthers, le formate de méthyle, le dioxyde de carbone et le trans-1,2 dichloroéthylène.
- Procédé selon l'une quelconque des revendications 1 à 3 caractérisé en ce que le fluide frigorigène comprend au moins un hydrofluorocarbure choisi parmi le 1,1,1,3,3-pentafluorobutane et le 1,1,1,3,3-pentafluoropropane.
- Procédé selon l'une quelconque des revendications 1 à 4 caractérisé en ce que le fluide frigorigène comprend au moins un hydrocarbure choisi parmi le pentane, l'isopentane et le cyclopentane.
- Procédé selon l'une quelconque des revendications 1 à 5 caractérisé en ce que le fluide frigorigène comprend de 40 à 100 % en poids de 1,1,1,4,4,4-hexafluorobut-2-ène et de 0 à 60 % en poids d'au moins un composé choisi parmi le pentane, l'isopentane, le cyclopentane et le trans-1,2,dichloroéthylène.
- Procédé selon l'une quelconque des revendications 1 à 6 caractérisé en ce que le fluide frigorigène comprend de 60 à 100 % en poids de 1,1,1,4,4,4-hexafluorobut-2-ène et de 0 à 40 % en poids de cyclopentane , pentane, d'isopentane ou trans 1,2-dichloroéthylène.
- Procédé selon l'une quelconque des revendications 1 à 7 caractérisé en ce que le fluide frigorigène comprend un stabilisant.
- Procédé selon l'une quelconque des revendications 1 à 8 caractérisé en ce que le fluide frigorigène comprend un lubrifiant.
- Procédé selon la revendication 9 caractérisé en ce que le lubrifiant est le le polyalkylène glycol, le polyolester ou le polyvinyl éther.
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
PL10745303T PL2459667T3 (pl) | 2009-07-28 | 2010-06-23 | Sposób przenoszenia ciepła |
EP17150137.2A EP3176239A1 (fr) | 2009-07-28 | 2010-06-23 | Procédé de transfert de chaleur |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR0955261A FR2948678B1 (fr) | 2009-07-28 | 2009-07-28 | Procede de transfert de chaleur |
PCT/FR2010/051279 WO2011015737A1 (fr) | 2009-07-28 | 2010-06-23 | Procede de transfert de chaleur |
Related Child Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP17150137.2A Division-Into EP3176239A1 (fr) | 2009-07-28 | 2010-06-23 | Procédé de transfert de chaleur |
EP17150137.2A Division EP3176239A1 (fr) | 2009-07-28 | 2010-06-23 | Procédé de transfert de chaleur |
Publications (2)
Publication Number | Publication Date |
---|---|
EP2459667A1 EP2459667A1 (fr) | 2012-06-06 |
EP2459667B1 true EP2459667B1 (fr) | 2017-02-22 |
Family
ID=41718600
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP17150137.2A Withdrawn EP3176239A1 (fr) | 2009-07-28 | 2010-06-23 | Procédé de transfert de chaleur |
EP10745303.7A Active EP2459667B1 (fr) | 2009-07-28 | 2010-06-23 | Procede de transfert de chaleur |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP17150137.2A Withdrawn EP3176239A1 (fr) | 2009-07-28 | 2010-06-23 | Procédé de transfert de chaleur |
Country Status (8)
Country | Link |
---|---|
US (3) | US20120117990A1 (fr) |
EP (2) | EP3176239A1 (fr) |
JP (3) | JP6021642B2 (fr) |
CN (1) | CN102471670B (fr) |
ES (1) | ES2619933T3 (fr) |
FR (1) | FR2948678B1 (fr) |
PL (1) | PL2459667T3 (fr) |
WO (1) | WO2011015737A1 (fr) |
Families Citing this family (24)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2937328B1 (fr) | 2008-10-16 | 2010-11-12 | Arkema France | Procede de transfert de chaleur |
FR2948678B1 (fr) * | 2009-07-28 | 2011-10-14 | Arkema France | Procede de transfert de chaleur |
FR2948679B1 (fr) | 2009-07-28 | 2011-08-19 | Arkema France | Procede de transfert de chaleur |
FR2968009B1 (fr) | 2010-11-25 | 2012-11-16 | Arkema France | Fluides frigorigenes contenant du (e)-1,1,1,4,4,4-hexafluorobut-2-ene |
US9157018B2 (en) | 2010-11-25 | 2015-10-13 | Arkema France | Compositions of chloro-trifluoropropene and hexafluorobutene |
FR2968310B1 (fr) | 2010-12-03 | 2012-12-07 | Arkema France | Compositions a base de 1,1,1,4,4,4-hexafluorobut-2-ene et de 3,3,4,4,4-pentafluorobut-1-ene |
MY161767A (en) | 2010-12-14 | 2017-05-15 | Du Pont | Combinations of e-1,3,3,3-tetrafluoropropene and at least one tetrafluoroethane and their use for heating |
TWI573971B (zh) | 2011-01-31 | 2017-03-11 | 杜邦股份有限公司 | 使用包含z-1,1,1,4,4,4-六氟-2-丁烯之工作流體製熱 |
FR2973809B1 (fr) * | 2011-04-08 | 2015-11-13 | Ceca Sa | Utilisation de zeolithes pour la stabilisation d'huiles |
FR2973717B1 (fr) * | 2011-04-08 | 2013-03-29 | Ceca Sa | Procede de reduction de l'acidite totale de compositions frigorigenes |
FR2977256B1 (fr) | 2011-07-01 | 2013-06-21 | Arkema France | Compositions de 2,4,4,4-tetrafluorobut-1-ene et de cis-1,1,1,4,4,4-hexafluorobut-2-ene |
FR2979419B1 (fr) | 2011-08-30 | 2018-03-30 | Arkema France | Fluides de transfert de chaleur supercritiques a base de tetrafluoropropene |
WO2013096515A1 (fr) * | 2011-12-21 | 2013-06-27 | E. I. Du Pont De Nemours And Company | Utilisation de compositions comprenant du e-1,1,1,4,4,5,5,5-octafluoro-2-pentène et éventuellement du 1,1,1,2,3-pentafluoropropane dans des cycles d'alimentation |
JP2015507666A (ja) * | 2011-12-21 | 2015-03-12 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニーE.I.Du Pont De Nemours And Company | 高温ヒートポンプでのe−1,1,1,4,4,5,5,5−オクタフルオロ−2−ペンテンおよび任意選択的に1,1,1,2,3−ペンタフルオロプロパンの使用 |
FR2989084B1 (fr) | 2012-04-04 | 2015-04-10 | Arkema France | Compositions a base de 2,3,3,4,4,4-hexafluorobut-1-ene |
US9234123B2 (en) * | 2013-03-21 | 2016-01-12 | Hsi Fire & Safety Group, Llc | Compositions for totally non-flammable aerosol dusters |
US20160138815A1 (en) * | 2014-11-17 | 2016-05-19 | Appollo Wind Technologies Llc | Isothermal-turbo-compressor-expander-condenser-evaporator device |
FR3033791B1 (fr) | 2015-03-18 | 2017-04-14 | Arkema France | Stabilisation du 1-chloro-3,3,3-trifluoropropene |
FR3046162B1 (fr) * | 2015-12-23 | 2019-12-13 | Arkema France | Procede de production et de purification du 2,3,3,3-tetrafluoro-1-propene. |
FR3056222B1 (fr) | 2016-09-19 | 2020-01-10 | Arkema France | Composition a base de 1-chloro-3,3,3-trifluoropropene |
JP2020514493A (ja) | 2017-03-20 | 2020-05-21 | ザ ケマーズ カンパニー エフシー リミテッド ライアビリティ カンパニー | トランス−1,1,1,4,4,4−ヘキサフルオロ−2−ブテンの組成物及び使用 |
FR3070982B1 (fr) | 2017-09-12 | 2019-08-30 | Arkema France | Composition a base d'hydrochlorofluoroolefine et d'huile minerale |
JP7444719B2 (ja) | 2020-07-10 | 2024-03-06 | ダイキン工業株式会社 | 2-クロロ-1,1-ジフルオロエタン(hcfc-142)、1,1,2-トリフルオロエタン(hfc-143)、及び(e)-1,2-ジフルオロエチレン(hfo-1132(e))及び/又は(z)-1,2-ジフルオロエチレン(hfo-1132(z))の製造方法 |
KR102620257B1 (ko) * | 2021-07-20 | 2024-01-03 | 주식회사 씨지아이 | 베이퍼 챔버 및 그에 사용되는 작동 유체 |
Family Cites Families (19)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2394762A2 (fr) * | 1977-06-17 | 1979-01-12 | Inst Tech Porc | Appareil de regulation de climat des locaux |
FR2511386A1 (fr) * | 1981-08-11 | 1983-02-18 | Inst Francais Du Petrole | Utilisation d'hydrocarbures chloro-fluores comme fluides de transfert de chaleur a temperature elevee |
US4948526A (en) * | 1989-09-26 | 1990-08-14 | Allied-Signal Inc. | Azeotrope-like compositions of pentafluorodimethyl ether and monochlorodifluoromethane |
DE10056606A1 (de) | 2000-11-15 | 2002-05-23 | Solvay Fluor & Derivate | Verwendung von Gemischen,die 1,1,1,3,3-Pentafluorbutan enthalten, als Kältemittel oder Wärmerträger |
US6913076B1 (en) * | 2002-07-17 | 2005-07-05 | Energent Corporation | High temperature heat pump |
US9005467B2 (en) * | 2003-10-27 | 2015-04-14 | Honeywell International Inc. | Methods of replacing heat transfer fluids |
KR101235583B1 (ko) | 2002-10-25 | 2013-02-22 | 허니웰 인터내셔널 인코포레이티드 | 플루오린 치환된 올레핀을 함유하는 조성물 |
JP4110388B2 (ja) | 2003-01-10 | 2008-07-02 | 荒川化学工業株式会社 | 金めっき部品用洗浄剤およびすすぎ剤並びに洗浄方法およびすすぎ方法 |
US7428816B2 (en) * | 2004-07-16 | 2008-09-30 | Honeywell International Inc. | Working fluids for thermal energy conversion of waste heat from fuel cells using Rankine cycle systems |
TWI708756B (zh) | 2005-06-24 | 2020-11-01 | 美商哈尼威爾國際公司 | 含有經氟取代之烯烴之組合物 |
CA3148429A1 (fr) * | 2005-11-01 | 2007-05-10 | The Chemours Company Fc, Llc | Compositions comprenant des olefines fluorees et leurs utilisations |
SG183045A1 (en) * | 2007-04-27 | 2012-08-30 | Du Pont | Azeotropic and azeotrope-like compositions of z-1,1,1,4,4,4-hexafluoro-2-butene |
BR122018074418B1 (pt) * | 2007-06-12 | 2019-03-26 | E. I. Du Pont De Nemours And Company | Composição e processo para produzir refrigeração |
WO2008157757A1 (fr) * | 2007-06-21 | 2008-12-24 | E. I. Du Pont De Nemours And Company | Procédé de détection de fuite dans un système de transport de chaleur |
US20090049856A1 (en) | 2007-08-20 | 2009-02-26 | Honeywell International Inc. | Working fluid of a blend of 1,1,1,3,3-pentafluoropane, 1,1,1,2,3,3-hexafluoropropane, and 1,1,1,2-tetrafluoroethane and method and apparatus for using |
MX2010002471A (es) * | 2007-09-06 | 2010-03-26 | Du Pont | Composiciones azeotropicas y similares a azeotropos de e-1,1,1,4,4,5,5,5-octafluoro-2-penteno. |
US20090095014A1 (en) * | 2007-10-12 | 2009-04-16 | Andrew Sun | Working fluid of a blend of 1,1,1,2-tetrafluoroethane, 1,1,1,2,3,3,3-heptafluoropropane, and 1,1,1,3,3,3-hexafluoropropane and method and apparatus for using |
EP2222746B1 (fr) * | 2007-12-19 | 2015-10-28 | E. I. du Pont de Nemours and Company | Compositions moussantes contenant un mélange azéotropique ou de type azéotropique contenant du z-1,1,1,4,4,4-hexafluoro-2-butène et du methyl formate et leurs applications dans la préparation de mousses à base de polyisocyanate |
FR2948678B1 (fr) * | 2009-07-28 | 2011-10-14 | Arkema France | Procede de transfert de chaleur |
-
2009
- 2009-07-28 FR FR0955261A patent/FR2948678B1/fr active Active
-
2010
- 2010-06-23 EP EP17150137.2A patent/EP3176239A1/fr not_active Withdrawn
- 2010-06-23 JP JP2012522206A patent/JP6021642B2/ja active Active
- 2010-06-23 ES ES10745303.7T patent/ES2619933T3/es active Active
- 2010-06-23 CN CN201080032948.5A patent/CN102471670B/zh active Active
- 2010-06-23 US US13/386,701 patent/US20120117990A1/en not_active Abandoned
- 2010-06-23 WO PCT/FR2010/051279 patent/WO2011015737A1/fr active Application Filing
- 2010-06-23 PL PL10745303T patent/PL2459667T3/pl unknown
- 2010-06-23 EP EP10745303.7A patent/EP2459667B1/fr active Active
-
2016
- 2016-07-06 JP JP2016133921A patent/JP2016197007A/ja active Pending
-
2018
- 2018-07-05 US US16/027,602 patent/US20190040292A1/en not_active Abandoned
- 2018-10-04 JP JP2018189123A patent/JP2019032155A/ja active Pending
-
2021
- 2021-05-27 US US17/332,261 patent/US20220119694A1/en not_active Abandoned
Non-Patent Citations (1)
Title |
---|
None * |
Also Published As
Publication number | Publication date |
---|---|
ES2619933T3 (es) | 2017-06-27 |
US20190040292A1 (en) | 2019-02-07 |
US20220119694A1 (en) | 2022-04-21 |
JP6021642B2 (ja) | 2016-11-09 |
JP2013500373A (ja) | 2013-01-07 |
EP2459667A1 (fr) | 2012-06-06 |
CN102471670A (zh) | 2012-05-23 |
JP2019032155A (ja) | 2019-02-28 |
JP2016197007A (ja) | 2016-11-24 |
WO2011015737A1 (fr) | 2011-02-10 |
CN102471670B (zh) | 2015-07-01 |
EP3176239A1 (fr) | 2017-06-07 |
FR2948678A1 (fr) | 2011-02-04 |
PL2459667T3 (pl) | 2017-06-30 |
US20120117990A1 (en) | 2012-05-17 |
FR2948678B1 (fr) | 2011-10-14 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
EP2459667B1 (fr) | Procede de transfert de chaleur | |
US10858561B2 (en) | Heat transfer method | |
EP2283102B1 (fr) | Compositions a base d'hydrofluoroolefines | |
EP2283103B1 (fr) | Compositions a base d'hydrofluoroolefines | |
EP2283101B1 (fr) | Compositions a base d'hydrofluoroolefines | |
EP2331651B1 (fr) | Fluide de transfert de chaleur | |
EP2459668A1 (fr) | Procede de transfert de chaleur | |
EP4146764A1 (fr) | Compositions de transfert de chaleur d'hydrofluorocarbones |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PUAI | Public reference made under article 153(3) epc to a published international application that has entered the european phase |
Free format text: ORIGINAL CODE: 0009012 |
|
17P | Request for examination filed |
Effective date: 20111222 |
|
AK | Designated contracting states |
Kind code of ref document: A1 Designated state(s): AL AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO PL PT RO SE SI SK SM TR |
|
DAX | Request for extension of the european patent (deleted) | ||
17Q | First examination report despatched |
Effective date: 20150428 |
|
GRAP | Despatch of communication of intention to grant a patent |
Free format text: ORIGINAL CODE: EPIDOSNIGR1 |
|
INTG | Intention to grant announced |
Effective date: 20161010 |
|
GRAS | Grant fee paid |
Free format text: ORIGINAL CODE: EPIDOSNIGR3 |
|
GRAA | (expected) grant |
Free format text: ORIGINAL CODE: 0009210 |
|
AK | Designated contracting states |
Kind code of ref document: B1 Designated state(s): AL AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO PL PT RO SE SI SK SM TR |
|
REG | Reference to a national code |
Ref country code: GB Ref legal event code: FG4D Free format text: NOT ENGLISH |
|
REG | Reference to a national code |
Ref country code: CH Ref legal event code: EP |
|
REG | Reference to a national code |
Ref country code: AT Ref legal event code: REF Ref document number: 869270 Country of ref document: AT Kind code of ref document: T Effective date: 20170315 |
|
REG | Reference to a national code |
Ref country code: IE Ref legal event code: FG4D Free format text: LANGUAGE OF EP DOCUMENT: FRENCH |
|
REG | Reference to a national code |
Ref country code: DE Ref legal event code: R096 Ref document number: 602010040203 Country of ref document: DE |
|
REG | Reference to a national code |
Ref country code: NL Ref legal event code: FP |
|
REG | Reference to a national code |
Ref country code: FR Ref legal event code: PLFP Year of fee payment: 8 |
|
REG | Reference to a national code |
Ref country code: LT Ref legal event code: MG4D |
|
REG | Reference to a national code |
Ref country code: ES Ref legal event code: FG2A Ref document number: 2619933 Country of ref document: ES Kind code of ref document: T3 Effective date: 20170627 |
|
REG | Reference to a national code |
Ref country code: AT Ref legal event code: MK05 Ref document number: 869270 Country of ref document: AT Kind code of ref document: T Effective date: 20170222 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: HR Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20170222 Ref country code: LT Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20170222 Ref country code: NO Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20170522 Ref country code: GR Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20170523 Ref country code: FI Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20170222 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: LV Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20170222 Ref country code: AT Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20170222 Ref country code: BG Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20170522 Ref country code: SE Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20170222 Ref country code: PT Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20170622 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: CZ Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20170222 Ref country code: SK Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20170222 Ref country code: RO Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20170222 Ref country code: EE Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20170222 |
|
REG | Reference to a national code |
Ref country code: DE Ref legal event code: R097 Ref document number: 602010040203 Country of ref document: DE |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: SM Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20170222 Ref country code: DK Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20170222 |
|
PLBE | No opposition filed within time limit |
Free format text: ORIGINAL CODE: 0009261 |
|
STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: NO OPPOSITION FILED WITHIN TIME LIMIT |
|
26N | No opposition filed |
Effective date: 20171123 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: MC Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20170222 |
|
REG | Reference to a national code |
Ref country code: CH Ref legal event code: PL |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: SI Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20170222 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: LI Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 20170630 Ref country code: LU Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 20170623 Ref country code: CH Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 20170630 |
|
REG | Reference to a national code |
Ref country code: FR Ref legal event code: PLFP Year of fee payment: 9 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: MT Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20170222 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: HU Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT; INVALID AB INITIO Effective date: 20100623 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: CY Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 20170222 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: MK Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20170222 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: AL Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20170222 Ref country code: IS Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20170622 |
|
P01 | Opt-out of the competence of the unified patent court (upc) registered |
Effective date: 20230524 |
|
PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: IT Payment date: 20230510 Year of fee payment: 14 Ref country code: IE Payment date: 20230510 Year of fee payment: 14 Ref country code: FR Payment date: 20230510 Year of fee payment: 14 Ref country code: DE Payment date: 20230502 Year of fee payment: 14 |
|
PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: TR Payment date: 20230620 Year of fee payment: 14 Ref country code: PL Payment date: 20230516 Year of fee payment: 14 |
|
PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: BE Payment date: 20230517 Year of fee payment: 14 |
|
PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: GB Payment date: 20230504 Year of fee payment: 14 Ref country code: ES Payment date: 20230711 Year of fee payment: 14 |
|
PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: NL Payment date: 20240515 Year of fee payment: 15 |